Tetrahydrofuran → HCID 86661959, compound

HRID 1912315Notes

Reaction equation

HRID 1912315 reaction equation
Cl[P:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])(Cl)=[O:3].[ClH:18].[CH3:19][O:20][C:21](=[O:25])[C@H:22]([CH3:24])[NH2:23].[CH2:26](N(CC)CC)C.C1COCC1>ClCCl>[Cl:18][C:8]1[C:7]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:6]([CH:11]=[CH:10][CH:9]=1)[O:5][P:2](=[N:23][C@H:22]([CH3:24])[C:21]([O:20][CH2:19][CH3:26])=[O:25])=[O:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2733257Alanine methyl ester hydrochlorideHCID 86661958Methyl 3-(2-(dichlorophosphoryloxy)phenyl)propanoate

Product 1

HCID 86661959HCID 86661959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 3-(2-(dichlorophosphoryloxy)phenyl)propanoate, 81 (2.77 mmol) and L-alanine methyl ester hydrochloride (0.42 g, 2.77 mmol) were suspended in anhydrous dichloromethane (10 mL). Anhydrous triethylamine (0.37 mL, 2.77 mmol) and dichloromethane (5 mL) were added dropwise at −78° C. under nitrogen. Following the addition, the reaction mixture was slowly warmed to it and stirred overnight. The solvent was removed under reduced pressure; the solid was washed with anhydrous ether (20 mL×2), and filtered. The filtrate was concentrated to a residue to give crude product as an oil. Dilution with THF (2.77 mL) gave a 1 M solution, which was used in the following step without any further purification.

Workup

  1. additionthe addition
  2. temperaturethe reaction mixture was slowly warmed to it
  3. customThe solvent was removed under reduced pressure
  4. washthe solid was washed with anhydrous ether (20 mL×2)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated to a residue
  7. customto give crude product as an oil

Sources & evidence

ORD record
ord-dd32b9dfc23b44a39cda93fb0d290234
Source dataset
uspto-grants-2013_12
Patent number
US08609627B2

Reaction notes

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